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1
Cardiolipin: a stereospecifically spin-labeled analogue and its specific enzymic hydrolysis.心磷脂：一种立体特异性自旋标记类似物及其特异性酶促水解
Proc Natl Acad Sci U S A. 1978 Mar;75(3):1227-31. doi: 10.1073/pnas.75.3.1227.
2
Photoreactive cardiolipin analogues.光反应性心磷脂类似物
Chem Phys Lipids. 1988 Aug;47(4):261-71. doi: 10.1016/0009-3084(88)90049-7.
3
Properties of an acid phosphatase in pulmonary surfactant.肺表面活性物质中一种酸性磷酸酶的特性
Proc Natl Acad Sci U S A. 1980 Feb;77(2):808-11. doi: 10.1073/pnas.77.2.808.
4
Age-related changes of the endogenous cardiolipin and plasmalogens of guinea pig kidney and their in vitro hydrolysis by endogenous phospholipases: a thin layer chromatographic analysis in conjunction with densitometric measurement.豚鼠肾脏内源性心磷脂和缩醛磷脂的年龄相关变化及其内源性磷脂酶的体外水解作用：结合光密度测量的薄层色谱分析
Cell Biochem Funct. 2003 Dec;21(4):337-44. doi: 10.1002/cbf.1035.
5
Synthesis and properties of phosphatidyl carnitine and phosphatidyl beta-methylcholine.磷脂酰肉碱和磷脂酰β-甲基胆碱的合成与性质
Lipids. 1975 Jan;10(1):20-4. doi: 10.1007/BF02532189.
6
Conversion of phosphatidylglycerol lipids to bis(monoacylglycero)phosphate in vivo.体内磷脂酰甘油脂质向双（单酰甘油）磷酸酯的转化。
Biochim Biophys Acta. 1980 Jun 23;618(3):407-19. doi: 10.1016/0005-2760(80)90259-3.
7
Spin label studies on the selectivity of lipid-protein interaction of cardiolipin analogues with the Na+/K+-ATPase.关于心磷脂类似物与钠钾ATP酶脂质-蛋白质相互作用选择性的自旋标记研究。
Biochim Biophys Acta. 1988 Jun 22;941(2):287-92. doi: 10.1016/0005-2736(88)90190-3.
8
Formation of molecular species of mitochondrial cardiolipin. 1. A novel transacylation mechanism to shuttle fatty acids between sn-1 and sn-2 positions of multiple phospholipid species.线粒体心磷脂分子物种的形成。1. 一种在多种磷脂物种的sn-1和sn-2位置之间穿梭脂肪酸的新型转酰基化机制。
Biochim Biophys Acta. 2009 Apr;1791(4):314-20. doi: 10.1016/j.bbalip.2009.01.004. Epub 2009 Jan 21.
9
Composition of cardiolipin molecular species in Escherichia coli.大肠杆菌中心磷脂分子种类的组成
J Bacteriol. 1980 Mar;141(3):1047-51. doi: 10.1128/jb.141.3.1047-1051.1980.
10
Synthesis of the diastereoisomers of 1,2-dipalmitoyl-sn-glycero-3-thiophosphorylethanolamine and their stereospecific hydrolysis by phospholipases A2 and C.1,2-二棕榈酰-sn-甘油-3-硫代磷酸乙醇胺非对映异构体的合成及其被磷脂酶A2和C的立体特异性水解
Biochemistry. 1982 Jun 22;21(13):3202-6. doi: 10.1021/bi00256a026.

引用本文的文献

1
Monolysocardiolipin: improved preparation with high yield.单心磷脂酰甘油：改进的高产制备方法。
J Lipid Res. 2011 Feb;52(2):389-92. doi: 10.1194/jlr.D010587. Epub 2010 Oct 19.
2
The Association of Cardiolipin with Detergent-solubilized Cytochrome c Oxidase.心磷脂与去污剂溶解的细胞色素c氧化酶的关联
Biophys J. 1982 Jan;37(1):108-9. doi: 10.1016/S0006-3495(82)84625-0.
3
pH-dissociation characteristics of cardiolipin and its 2'-deoxy analogue.心磷脂及其2'-脱氧类似物的pH解离特性。
Lipids. 1993 Oct;28(10):877-82. doi: 10.1007/BF02537494.
4
Composition of cardiolipin molecular species in Escherichia coli.大肠杆菌中心磷脂分子种类的组成
J Bacteriol. 1980 Mar;141(3):1047-51. doi: 10.1128/jb.141.3.1047-1051.1980.
5
Properties of an acid phosphatase in pulmonary surfactant.肺表面活性物质中一种酸性磷酸酶的特性
Proc Natl Acad Sci U S A. 1980 Feb;77(2):808-11. doi: 10.1073/pnas.77.2.808.
6
ESR spin-label studies of lipid-protein interactions in membranes.膜中脂-蛋白相互作用的电子自旋共振自旋标记研究。
Biophys J. 1982 Jan;37(1):265-74. doi: 10.1016/S0006-3495(82)84675-4.

本文引用的文献

1
STUDIES ON HYDROLYSIS OF CARDIOLIPIN BY SNAKE VENOM PHOSPHOLIPASE A.蛇毒磷脂酶A对心磷脂水解作用的研究
J Biochem. 1965 Apr;57:529-38. doi: 10.1093/oxfordjournals.jbchem.a128111.
2
ON THE STRUCTURE OF CARDIOLIPIN.论心磷脂的结构。
Biochemistry. 1964 Jul;3:976-80. doi: 10.1021/bi00895a023.
3
THE STEREOCHEMICAL CONFIGURATION OF PHOSPHATIDYL GLYCEROL.磷脂酰甘油的立体化学构型
Biochim Biophys Acta. 1964 Feb 24;84:106-8. doi: 10.1016/0926-6542(64)90110-6.
4
A rapid method of total lipid extraction and purification.一种快速的总脂质提取与纯化方法。
Can J Biochem Physiol. 1959 Aug;37(8):911-7. doi: 10.1139/o59-099.
5
The phosphatide composition of a purified cytochrome oxidase preparation.一种纯化的细胞色素氧化酶制剂的磷脂组成。
J Biol Chem. 1958 Sep;233(3):740-2.
6
Phosphatides of pig heart cell fractions.猪心脏细胞组分的磷脂
J Biol Chem. 1958 Sep;233(3):562-5.
7
A note of the asymmetrical metabolism of glycerol.甘油不对称代谢的一则笔记。
J Biol Chem. 1954 Dec;211(2):963-7.
8
Studies on cardiolipin. 3. Structural identity of ox-heart cardiolipin and synthetic diphosphatidyl glycerol.关于心磷脂的研究。3. 牛心磷脂与合成二磷脂酰甘油的结构一致性。
Biochim Biophys Acta. 1966 Feb 1;116(1):114-24. doi: 10.1016/0005-2760(66)90097-x.
9
Synthesis of fatty acid anhydrides by reaction with dicyclohexylcarbodiimide.通过与二环己基碳二亚胺反应合成脂肪酸酐。
J Lipid Res. 1966 Jan;7(1):174-5.
10
Molecular motion in spin-labeled phospholipids and membranes.自旋标记磷脂和膜中的分子运动。
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心磷脂：一种立体特异性自旋标记类似物及其特异性酶促水解

Cardiolipin: a stereospecifically spin-labeled analogue and its specific enzymic hydrolysis.

作者信息

Cable M B, Jacobus J, Powell G L

出版信息

Proc Natl Acad Sci U S A. 1978 Mar;75(3):1227-31. doi: 10.1073/pnas.75.3.1227.

DOI:10.1073/pnas.75.3.1227
PMID:274715
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC411443/
Abstract

The spin-labeled cardiolipin 1-(3-sn-phosphatidyl)-3-[1-acyl-2-(16-doxylstearoyl)glycero(3)phosphol]-sn-glycerol has been prepared. The stereoselective synthesis makes use of the monolysocardiolipin 1-(3-sn-phosphatidyl)-3-[1-acyl-2-lyso-sn-glycero(3)phospho]-sn-glycerol, available from the stereospecific hydrolysis of cardiolipin by phospholipase A2 (phosphatide 2-acylhydrolase, EC 3.1.1.4) of Trimeresurus flavoviridis. The results of treatment of the spin-labeled cardiolipin with the cardiolipin-specific phospholipase D (phosphatidylcholine phosphatidohydrolase, EC 3.1.4.4) (Hemophilus parainfluenzae) of known specificity and with phospholipase C (phosphatidylcholine cholinephosphohydrolase, EC 3.1.4.3) of Bacillus cereus are consistent with the assigned structure. The spin-labeled cardiolipin is further characterized and the unique features of this diastereomer are discussed in the context of the unusual stereochemistry of the natural phospholipid.

摘要

已制备出自旋标记的心磷脂1-(3 - sn - 磷脂酰)-3-[1 - 酰基 - 2-(16 - 二氧硬脂酰)甘油(3)磷脂]-sn - 甘油。该立体选择性合成利用了单溶血心磷脂1-(3 - sn - 磷脂酰)-3-[1 - 酰基 - 2 - 溶血 - sn - 甘油(3)磷酸]-sn - 甘油，其可通过竹叶青蛇的磷脂酶A2（磷脂2 - 酰基水解酶，EC 3.1.1.4）对心磷脂进行立体特异性水解获得。用已知特异性的嗜副流感嗜血杆菌的心磷脂特异性磷脂酶D（磷脂酰胆碱磷脂水解酶，EC 3.1.4.4）和蜡状芽孢杆菌的磷脂酶C（磷脂酰胆碱胆碱磷酸水解酶，EC 3.1.4.3）处理自旋标记的心磷脂的结果与所指定的结构一致。对自旋标记的心磷脂进行了进一步表征，并结合天然磷脂不寻常的立体化学对该非对映异构体的独特特征进行了讨论。